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Informal Italian restaurant serving pasta, seafood & meat dishes, plus desserts & a large wine list.
Hours
| Monday | Closed |
| Tuesday | 5–9 PM |
| Wednesday | 5–9 PM |
| Thursday | 5–9 PM |
| Friday | 5–9 PM |
| Saturday | 5–9 PM |
| Sunday | Closed |
Address and Contact Information
Address: 85 Free St, Portland, ME 04101
Phone: (207) 808-8623
Website: https://leewardmaine.com/
Menu Photos
Order and Reservations
Reservations: resy.com
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Leeward
Pasta and Good Times in Portland, Maine.
Leeward (@leewardmaine) · Portland, ME – Instagram
pasta & good times tuesday-saturday 5-9pm reservations via @resy bar is always saved for walk-ins if you prefer walkin’ in.
Book Your Leeward Reservation Now on Resy
Leeward is a full-service restaurant with an Italian bent and a fondness for fresh pasta … Leeward. 85 Free St. 85 Free Street. Portland, ME 04101. Get …
Reviews
Kira “NYC foodie”
We really enjoyed our dining experience here. The host and server were great, our server made some great recommendations such as the gnocchi dish which was AMAZING, the best I’ve ever had. The fig salad and lobster sphegettini were lovely as well.
… moreChad Klinefelter
EDIT:
Adding more to my original review having returned to Leeward more than once – it is a top restaurant in Portland. This time around, the order included the sacchettoni, the halibut, and some exceptional asparagus. Oh, and the gnocco fritto, *always* !
ORIGINAL REVIEW:
Excellent all around. I would describe the menu as Italian-inspired, given that their big thing is their homemade pasta, but it’s more of a modern menu as opposed to one of traditional Italian dishes.
For the starters: the gnocco fritto are a MUST-have. The roasted black salsify root was also fantastic – salsify root being a root veggie that’s something between a parsnip and a potato. That plate was practically licked clean.
For the mains: we went all pasta, though they do have a few larger “secondi” type plates. We had the sunchoke & goat cheese agnolotti (stuffed pasta), and the rigatoni with beef & pork ragù bolognese.
They had a good drink menu with a nice array of wines and cocktails, as well as nice mocktails.
For dessert, we had the plum sorbetto, as well as the best-dressed carrot cake I’ve ever had (topped with candied pecans, fresh blood orange, candied ginger, candied zest, rosemary).
We sat at the chef’s counter, which was amazing, because we got to see all of our food being prepared. We observed a super well-run kitchen, with staff seeming to be enjoying themselves, which made the food taste even better, as we were able to appreciate the effort put into it. It was also fun to see the other dishes on the menu being prepared and plated, plus being able to see what the most popular dishes were (the gnocco fritto was a common one, and for good reason).
The atmosphere and service were both great – our server was Molly.
Be prepared to spend (after tax & tip) upwards of $100 per person – note though that we ordered starters, mains, drinks, and desserts though, so quite a full sampling.
… moreAdding more to my original review having returned to Leeward more than once – it is a top restaurant in Portland. This time around, the order included the sacchettoni, the halibut, and some exceptional asparagus. Oh, and the gnocco fritto, *always* !
ORIGINAL REVIEW:
Excellent all around. I would describe the menu as Italian-inspired, given that their big thing is their homemade pasta, but it’s more of a modern menu as opposed to one of traditional Italian dishes.
For the starters: the gnocco fritto are a MUST-have. The roasted black salsify root was also fantastic – salsify root being a root veggie that’s something between a parsnip and a potato. That plate was practically licked clean.
For the mains: we went all pasta, though they do have a few larger “secondi” type plates. We had the sunchoke & goat cheese agnolotti (stuffed pasta), and the rigatoni with beef & pork ragù bolognese.
They had a good drink menu with a nice array of wines and cocktails, as well as nice mocktails.
For dessert, we had the plum sorbetto, as well as the best-dressed carrot cake I’ve ever had (topped with candied pecans, fresh blood orange, candied ginger, candied zest, rosemary).
We sat at the chef’s counter, which was amazing, because we got to see all of our food being prepared. We observed a super well-run kitchen, with staff seeming to be enjoying themselves, which made the food taste even better, as we were able to appreciate the effort put into it. It was also fun to see the other dishes on the menu being prepared and plated, plus being able to see what the most popular dishes were (the gnocco fritto was a common one, and for good reason).
The atmosphere and service were both great – our server was Molly.
Be prepared to spend (after tax & tip) upwards of $100 per person – note though that we ordered starters, mains, drinks, and desserts though, so quite a full sampling.
Emily Palmer
Leeward is a must stop restaurant any time we are in Portland. The menu is delicious and the chef does an excellent job of highlighting the season. They do a great job with gluten free, offering gnocchi as a substitution that is just as good as the regular stuff. We’ll be back!
… moreJames Stephen Shaw
Leeward was outstanding.
I had “fusilli, black trumpet mushrooms, corn crema, caramelized shallots, radicchio, lemon thyme”.. The corn crema sauce was quite subtle distinctive and lovely.The Waitress explained it had mascarpone in the sauce which made it rich without being goopy
My wife had “cannelloni, sheep’s milk ricotta, chanterelle mushrooms, parmigiano-reggiano” – also excellent and very different in flavor from mine
For dessert I had panna cotta with chocolate sauce and fresh figs brulee. It was wonderfully earthy, not sweet, with layers of flavors.
Came back again 5/6/25. Another wonderful dinner here (which I chose for my birthday). The surprise highlight was an unforgettable “savoy cabbage salad, anchovy-horseradish vinaigrette, pecorino, purple daikon, seeds & grains”. Amazing texture and taste.
… moreI had “fusilli, black trumpet mushrooms, corn crema, caramelized shallots, radicchio, lemon thyme”.. The corn crema sauce was quite subtle distinctive and lovely.The Waitress explained it had mascarpone in the sauce which made it rich without being goopy
My wife had “cannelloni, sheep’s milk ricotta, chanterelle mushrooms, parmigiano-reggiano” – also excellent and very different in flavor from mine
For dessert I had panna cotta with chocolate sauce and fresh figs brulee. It was wonderfully earthy, not sweet, with layers of flavors.
Came back again 5/6/25. Another wonderful dinner here (which I chose for my birthday). The surprise highlight was an unforgettable “savoy cabbage salad, anchovy-horseradish vinaigrette, pecorino, purple daikon, seeds & grains”. Amazing texture and taste.
Chris Hamilton
This is our second time coming here and it was absolutely exquisite both times. We had the squash bloosom apatizer.Fried in the lightest of batters it was so good. Between that and the two house made pasta dishes we had we moon with flavor and deliciousness. If your in portland check this place out, you wont be disappointed.
… moreAudrey Friedman
The food is pretty solid, we ordered the focaccia with balsamic with was phenomenal and then for entrees we ordered the butternut squash risotto and rigatoni with pork. I enjoyed both. I do wish there were a few more traditional Italian items on the menu but we were overall happy with our meals.
For dessert we had the butterscotch cranberry tart and the cinnamon apple gelato – both seasonal items I believe. Excellent, especially the gelato!
The bill for two was about $112. I don’t see myself becoming a frequent visitor but I’d definitely be interested in checking out the seasonal options in the future from time to time.
Staff were all lovely and friendly!
… moreFor dessert we had the butterscotch cranberry tart and the cinnamon apple gelato – both seasonal items I believe. Excellent, especially the gelato!
The bill for two was about $112. I don’t see myself becoming a frequent visitor but I’d definitely be interested in checking out the seasonal options in the future from time to time.
Staff were all lovely and friendly!
Audrey D
Leeward was such a delightful treat! Reservations are recommended as they fill up fast. We loved their flavorful and fun mocktails. The menu is small and constantly updated based on what is in season. It made it easy to decide what to order. For appetizers we got the focaccia and fried artichoke hearts. The focaccia was soft and balanced with a saltiness that paired beautifully well with the olive oil. The artichokes were tender and lightly battered. I ordered the mushroom ricotta pasta and my husband ordered the braised rabbit pasta. This place is known for their pasta dishes and did not disappoint! My favorite dessert was the hazelnut tart. We had such a good time overall. Service was efficient, the waitstaff was prompt and helpful, and we left having had a perfect amount of food for a fun night out. I highly recommend Leeward!
… morePriscilla Arsenault
Food is fresh, staff is friendly & knowledgeable, space is open & inviting, loved the background music that was playing!
… moreVictoria Hernandez
Wow! What an amazing experience! The atmosphere is warm and welcoming from the moment we were greeted. Maddy, our server, was such a pleasure! And we do hold that high on the list of important aspects of dining out, which we do a lot. Then came the drinks from the menu which were soooo delish! And oh the fooood Everything we ordered was perfection!
… moreGina Fox
Fantastic fresh pasta and food with a some twists and tweaks. The gnocco frito, grilled cabbage, choc tagliatelle, agnolotti and pork were all outstanding. And the choc cake was to die for!
Above all wonderful service: at the end of the night when everyone was gone except 1 bar patron instead of rushing us out and clearing everything they brought us 2 fresh bottles of water!!
… moreAbove all wonderful service: at the end of the night when everyone was gone except 1 bar patron instead of rushing us out and clearing everything they brought us 2 fresh bottles of water!!